EP2953610B1 - Semi-permanent hair straightening composition and method - Google Patents

Semi-permanent hair straightening composition and method Download PDF

Info

Publication number
EP2953610B1
EP2953610B1 EP14705651.9A EP14705651A EP2953610B1 EP 2953610 B1 EP2953610 B1 EP 2953610B1 EP 14705651 A EP14705651 A EP 14705651A EP 2953610 B1 EP2953610 B1 EP 2953610B1
Authority
EP
European Patent Office
Prior art keywords
composition
hair
acid
curly
alkyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
EP14705651.9A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP2953610A1 (en
Inventor
Murat KADIR
Mark J. MCGUINESS
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Lubrizol Advanced Materials Inc
Original Assignee
Lubrizol Advanced Materials Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Lubrizol Advanced Materials Inc filed Critical Lubrizol Advanced Materials Inc
Publication of EP2953610A1 publication Critical patent/EP2953610A1/en
Application granted granted Critical
Publication of EP2953610B1 publication Critical patent/EP2953610B1/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/04—Preparations for permanent waving or straightening the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners

Definitions

  • the exemplary embodiment relates to a method for straightening hair by application of heat to hair coated with a composition comprising ethylene carbonate.
  • hydroxide base which replaces the disulfide bonds (-CH 2 -S-S-CH 2 -) with lanthionine bonds (-CH 2 -S-CH 2 -) in a two stage process using a hydroxide ion in the first step and a thiol group in the second.
  • the hydroxide is used at fairly high concentrations and can cause scalp burning, and irritation or damage of the eyes and nose. Thiols leave the hair with an unpleasant odor and can lead to degradation of the hair fibers.
  • Semi-permanent methods use a cross-linking agent to form bonds while the hair is heated.
  • Formaldehyde for example, is used in many commercial straightening products, either as an ingredient of the composition or as a reaction product that is formed on heating of the hair. However, it can cause allergic reactions to the skin, eyes and lungs, can cause severe damage to the eyes, and poses other health risks.
  • the use of formaldehyde in hair straightening compositions has been discouraged or banned in some countries but it remains in widespread use, due to its effectiveness. Relaxing compositions including a denaturing agent such as urea have also been proposed.
  • urea is less caustic than a hydroxide-based composition, it can decompose to ammonia and poisonous isocyanic acid at the high temperatures used for thermal hair straightening.
  • US 2008/00775681 relates to a hair shaping composition that contains a N-alkyl-2-mercaptoacetamide as an active hair straightening compound in combination with a hair swelling or penetration agent selected from a myriad of compounds including propylene carbonate.
  • JP 2007-176796 concerns a fizzy hair straightening agent composition comprising an inositol phosphoric acid derivative (active hair straightening compound), ethanol, and numerous optional hair penetration enhancing agents including an alkylene carbonates/ derivatives.
  • compositions require a primary hair straightening component in combination with a hair penetration agent to facilitate the penetration of the active component into the hair fiber.
  • US 3,966,903 relates to a hair-waving composition containing a sulfite or bisulfite as the active hair-waving compound and a wave accelerating agent including an alkylene carbonate.
  • the alkylene carbonate is utilized as a hair swelling or penetrating agent which opens-up the hair fiber which permits the active sulfite or bisulfite active hair-waving agent better access to the cysteine linkages situated within the "opened" hair fiber.
  • FR 2 847 473 discloses an oxazolidinone for use as a cosmetic and a drug.
  • the disclosed oxazolidinones inhibit the migration of cells involved in the immune/inflammatory/irritant response.
  • the composition including the disclosed oxazolidinones are used particularly in dermatological applications.
  • DE 10 2005 017 913 concerns a hair treatment composition that is in the form of a paste.
  • the paste is prepared from three components: a) at least one cyclic carbonate; b) at least one nonionic surfactant; and c) at least one silicate.
  • the paste is used as a base for formulating hair coloring agents (dyes or dye precursors).
  • WO 2013/125053 relates to a heat transfer dying process for hair.
  • the dye composition includes at least one natural dye or dye precursor and at least one organic compound which is liquid at 25°C, an atmospheric pressure of 0.101 Pa (760 mmHg), and with a Hansen solubility parameter of less than 16 MPa1/2 at 25°C.
  • organic compounds including alkylene carbonates are disclosed. The purpose of the organic compound is to function as a solvent.
  • the present invention relates to
  • the invention further relates to
  • thermoally-activated agent ethylene carbonate
  • the present invention relates to a process and method of using a hair straightening composition.
  • the composition includes the one thermally-activated agent which can be present, in total, at up to 95 wt. % or up to 70 wt. % of the composition and may further include a solvent/diluent in which the thermally-activated agent is soluble or dispersible.
  • thermally-activated it is meant that the agent is activated by heat, as in a hair-straightening process.
  • the composition may be in the form of a liquid, cream, mousse, gel, spray, or the like.
  • the process for straightening keratin fibers includes contacting the keratin fibers with the composition to coat the fibers, maintaining the keratin-fibers in contact with the composition for sufficient time to effect straightening when the fibers are heated, and optionally drying the fibers to remove at least some of the solvent.
  • the keratin fibers, coated with the composition are contacted with a surface of a heating device, i.e. a flat iron, having a temperature of at least 200 °C for sufficient time to relax the keratin fibers, e.g., by reaching the glass transition temperature, which can vary, to some degree, depending on the moisture content.
  • the relaxation generally results in an increase in the average length of the keratin fibers, as measured when a lock of the curly fibers is suspended from a support, of at least 5% or at least 10%, which can be maintained over several hair washing treatments (involving shampooing and drying the hair), such as at least 10 or at least 20 washes.
  • the exemplary process is semi-permanent in that over time, the straightened fibers begin to return to their original, curly state. While the method can be used to form very straight hair, it can also be used in a process in which a semi-permanent wave is created.
  • alkylene carbonates have the general formula shown as Structure (I): where
  • n 0, i.e., the structure represents a five-membered ring of the general formula shown as Structure (II): where A, R and R' are as defined above.
  • the alkylene carbonate can be of the general form of Structure (III): where R is as above.
  • EC ethylene carbonate
  • Exemplary thermally-activated agent(s) according to structure (I) are small molecules (MW ⁇ 800 g/mol, or ⁇ 600 g/mol, such as ⁇ 200 g/mol) rather than oligomeric compounds or polymers ( ⁇ 1000 g/mol). They are water compatible and stable, able to penetrate and react with keratinous materials, and can be activated by a flat or round iron at ⁇ 210°C.
  • the thermally-activated agent i.e. ethylene carbonate (1,3-dioxolan-2-one) according to structure (I) is present in the straightening composition at a concentration of at least 5 wt.%, or at least 7 wt.%., or at least 10 wt.%, or at least 12 wt.%, or at least 15 wt.%, or at least 18 wt.%, and in some embodiments, the thermally-activated agent is present in the straightening composition at a concentration of up to 95 wt.%, or up to 70 wt.%, or up to 55 wt.%, or up to 50 wt.%, or up to 40 wt. %, or up to 35 wt.%, or up to 30 wt.%.
  • the thermally-activated agent may suitably be present in the composition at a total concentration of 10-40 wt.%, or at least 15 wt.%.
  • the thermally-activated agent includes a mixture of ethylene carbonate and propylene carbonate at a weight ratio of from 95/5 to 5/95, such as at least 10/90.
  • the propylene carbonate may replace some or all of other solvents used in the composition.
  • JEFFSOL® alkylene carbonates suitable for use herein are available from Huntsman Corporation under the tradename JEFFSOL® alkylene carbonates.
  • JEFFSOL ethylene carbonate is solid at room temperature.
  • JEFFSOL EC-75, EC-50, and EC-25 are blends of JEFFSOL ethylene carbonate and propylene carbonate in the ratios of 75/25, 50/50 and 25/75 by weight, respectively. These blends are liquid at room temperature. As sold, these products are said to be at least 99.8% pure. Higher purity versions are also available.
  • U.S. Patent No. 2,873,282 describes methods for making alkylene carbonates by reacting an alkylene oxide or compound thereof with carbon dioxide.
  • U.S. Patent No. 2,773,070 describes similar methods.
  • an alkylammonium halide catalyst such as tetraethylammonium bromide is employed.
  • Glycerol (glycerin) carbonate (GC) is available commercially and can be synthesized by the reaction of glycerin with a carbonate source such as phosgene, a dialkyl carbonate, or an alkylene carbonate; by reaction of glycerin with urea, carbon dioxide, and oxygen; or by reaction of carbon dioxide with glycidol.
  • the composition (and treatment process described herein) is free or substantially free (less than 1 wt. %, such as less than 0.1 wt. %) of thermally-activated agents/cross-linking agents other than ethylene carbonate.
  • ethylene carbonate is the sole thermally-activated agent.
  • the composition and method are free or substantially free of formaldehyde.
  • the exemplary method and composition use no formaldehyde either directly, in the composition, or through reaction, during the method, of any sources of formaldehyde.
  • the composition and process may be free or substantially free of glyoxylic acid, urea, and derivatives thereof, which can break down to form irritants.
  • the composition (and treatment process described herein) is free or substantially free (less than 1 wt. %, or less than 0.1 wt. %, or less than 0.01 wt. %) of cyclic mercapto (thiol) group-containing compounds.
  • Cyclic mercapto group-containing compounds are cyclic compounds containing an S-H group linked directly to a ring carbon atom.
  • the composition (and treatment method described herein) is free or substantially free (less than 1 wt. %, such as less than 0.1 wt. %) of all compounds which contain thiol groups, including aliphatic and cyclic thiol group-containing compounds.
  • the process is free of sulfites which can break the bisulfide bond in the keratin fibers (that are typically used in permanent waving compositions).
  • the composition may include a solvent in which the thermally-activated agent(s) is soluble/dispersible.
  • the solvent may be selected from water, alcohols and combinations thereof. Specific examples include water and/or ethanol.
  • composition can be prepared as water-free or water-based formulations, and formulations containing water-miscible auxiliary solvents and/or diluents are also contemplated.
  • Useful solvents commonly employed are typically liquids, such as water (deionized, distilled or purified), alcohols, such as C 1 -C 10 aliphatic and aromatic alcohols (including diols and triols, such as glycols, e.g., ethylene glycol, propylene glycol, and glycerin), polyols, and the like, and mixtures thereof.
  • solvents other than water
  • linear and branched alcohols such as ethanol, propanol, isopropanol, hexanol, and the like
  • aromatic alcohols such as benzyl alcohol, cyclohexanol, and the like.
  • Non-limiting examples of polyols include polyhydroxy alcohols, such as glycerin, propylene glycol, butylene glycol, hexylene glycol, C 2 to C 4 alkoxylated alcohols and C 2 to C 4 alkoxylated polyols, such as ethoxylated, propoxylated, and butoxylated ethers of alcohols, diols, and polyols having about 2 to about 30 carbon atoms and 1 to about 40 alkoxy units, polypropylene glycol, polybutylene glycol, and the like.
  • polyhydroxy alcohols such as glycerin, propylene glycol, butylene glycol, hexylene glycol, C 2 to C 4 alkoxylated alcohols and C 2 to C 4 alkoxylated polyols, such as ethoxylated, propoxylated, and butoxylated ethers of alcohols, diols, and polyols having about 2 to about 30 carbon atoms and
  • non-aqueous solvents or diluents include silicones, and silicone derivatives, such as cyclomethicone, and the like, ketones such as acetone and methylethyl ketone; natural and synthetic oils and waxes, such as vegetable oils, plant oils, animal oils, essential oils, mineral oils, C 7 to C 40 isoparaffins, alkyl carboxylic esters, such as ethyl acetate, amyl acetate, ethyl lactate, and the like, jojoba oil, shark liver oil, and the like.
  • Some of the foregoing non-aqueous auxiliary solvents or diluents may also serve as conditioners and emulsifiers. For purposes of computing a weight basis in the composition, however, all of the liquids listed in this section are considered as solvents/diluents.
  • the pH of the composition can be from to 1.5-9.5, e.g., at least 4.5, or at least 5.5. In some embodiments, the pH is up to 8.5, or up to 7.5, or up to 6.5. To provide the selected pH, the composition may include one or more pH modifiers selected from organic and inorganic acids and bases.
  • Acidic materials include organic acids and inorganic acids, in particular, monocarboxylic acids, dicarboxylic acids, and tricarboxylic acids, for example, acetic acid, citric acid, tartaric acid, alpha-hydroxy acids, beta-hydroxy acids, salicylic acid, lactic acid, malic acid, glycolic acid, amino acids, and natural fruit acids, or inorganic acids, for example, hydrochloric acid, nitric acid, sulfuric acid, sulfamic acid, phosphoric acid, and combinations thereof.
  • Basic materials include inorganic and organic bases, and combinations thereof.
  • inorganic bases include but are not limited to the alkali metal hydroxides (especially sodium, potassium, and ammonium), and alkali metal salts such as sodium borate (borax), sodium phosphate, sodium pyrophosphate, and the like; and mixtures thereof.
  • organic bases examples include triethanolamine (TEA), diisopropanolamine, triisopropanolamine, aminomethyl propanol, dodecylamine, cocamine, oleamine, morpholine, triamylamine, triethylamine, tetrakis(hydroxypropyl)ethylenediamine, L-arginine, aminomethyl propanol, tromethamine (2-amino 2-hydroxymethyl-1,3-propanediol), and PEG-15 cocamine.
  • Such pH modifiers may be present at from 0.0001 wt. % to 50 wt. %, based on the active component.
  • the composition may include one or more auxiliary components, such as rheology modifiers, surfactants, emulsifiers, conditioning agents, humectants, emollients, preservatives, chelating agents, propellants, fragrance, botanicals, hair fixing agents, colorants, combinations thereof, and the like.
  • auxiliary components such as rheology modifiers, surfactants, emulsifiers, conditioning agents, humectants, emollients, preservatives, chelating agents, propellants, fragrance, botanicals, hair fixing agents, colorants, combinations thereof, and the like.
  • the composition can include a rheology modifier which increases the overall viscosity of the composition.
  • the viscosity of the composition, when applied to the hair can be at least 400 mPa ⁇ s (cPs), or at least 1000 mPa ⁇ s (cPs), or at least 2000 mPa ⁇ s (cPs), or at least 3000 mPa ⁇ s (cPs), and can be up to 10,000 mPa ⁇ s (cPs).
  • the composition may include one or more rheology modifiers, which can be synthetic or natural.
  • Examples include fatty alcohols, such as C 10 -C 32 alcohols, e.g., C 12 -C 22 alcohols, natural oils, and polymers of acrylic acid and/or methacrylic acid, such as carbomers.
  • exemplary natural oils include mineral oils (mainly C 15 -C 40 linear and branched aliphatic alkanes, with minor amounts of cycloalkanes), which may be sold as paraffinum liquidum.
  • Exemplary synthetic rheology modifiers include acrylic based polymers and copolymers.
  • One class of acrylic based rheology modifiers are the carboxyl functional alkali-swellable and alkali-soluble thickeners (ASTs) produced by the free-radical polymerization of acrylic acid alone or in combination with other ethylenically unsaturated monomers.
  • the polymers can be synthesized by solvent/precipitation as well as emulsion polymerization techniques.
  • Exemplary synthetic rheology modifiers of this class include homopolymers of acrylic acid or methacrylic acid and copolymers polymerized from one or more monomers of acrylic acid, substituted acrylic acid, and salts and C 1 -C 30 alkyl esters of acrylic acid and substituted acrylic acid.
  • the substituted acrylic acid contains a substituent positioned on the alpha and/or beta carbon atom of the molecule, wherein in one aspect the substituent is independently selected from C 1-4 alkyl, -CN, and -COOH.
  • substituent is independently selected from C 1-4 alkyl, -CN, and -COOH.
  • other ethylenically unsaturated monomers such as, for example, styrene, vinyl acetate, ethylene, butadiene, acrylonitrile, as well as mixtures thereof can be copolymerized into the backbone.
  • the foregoing polymers are optionally crosslinked by a monomer that contains two or more moieties that contain ethylenic unsaturation.
  • the crosslinker is selected from a polyalkenyl polyether of a polyhydric alcohol containing at least two alkenyl ether groups per molecule.
  • Other Exemplary crosslinkers are selected from allyl ethers of sucrose and allyl ethers of pentaerythritol, and mixtures thereof. These polymers are more fully described in U.S. Patent No. 5,087,445 ; U.S. Patent No. 4,509,949 ; and U.S. Pat. No. 2,798,053 .
  • the AST rheology modifier or thickener is a crosslinked homopolymer polymerized from acrylic acid or methacrylic acid and is generally referred to under the INCI name of Carbomer.
  • Commercially available Carbomers include Carbopol® polymers 934, 940, 941, 956, 980, and 996 available from Lubrizol Advanced Materials, Inc.
  • the rheology modifier is selected from a crosslinked copolymer polymerized from a first monomer selected from one or more monomers of acrylic acid, substituted acrylic acid, salts of acrylic acid and salts of substituted acrylic acid and a second monomer selected from one or more C 10 -C 30 alkyl acrylate esters of acrylic acid or methacrylic acid.
  • the monomers can be polymerized in the presence of a steric stabilizer such as disclosed in U.S. Patent No. 5,288,814 .
  • a steric stabilizer such as disclosed in U.S. Patent No. 5,288,814 .
  • Some of the forgoing polymers are designated under INCI nomenclature as Acrylates/C10-30 Alkyl Acrylate Crosspolymer and are commercially available under the trade names Carbopol® 1342 and 1382, Carbopol® Ultrez 20 and 21, Carbopol® ETD 2020 and Pemulen® TR-1 and TR-2 from Lubrizol Advanced Materials, Inc.
  • the auxiliary rheology modifier can be a crosslinked, linear poly(vinyl amide/acrylic acid) copolymer as disclosed in U.S. Patent No. 7,205,271 .
  • HASE hydrophobically modified alkali-swellable and alkali-soluble emulsion
  • Typical HASE polymers are free radical addition polymers polymerized from pH sensitive or hydrophilic monomers (e.g., acrylic acid and/or methacrylic acid), hydrophobic monomers (e.g., C 1 -C 30 alkyl esters of acrylic acid and/or methacrylic acid, acrylonitrile, styrene), an "associative monomer", and an optional crosslinking monomer.
  • the associative monomer comprises an ethylenically unsaturated polymerizable end group, a non-ionic hydrophilic midsection that is terminated by a hydrophobic end group.
  • the non-ionic hydrophilic midsection comprises a polyoxyalkylene group, e.g., polyethylene oxide, polypropylene oxide, or mixtures of polyethylene oxide/polypropylene oxide segments.
  • the terminal hydrophobic end group is typically a C 8 -C 40 aliphatic moiety.
  • Exemplary aliphatic moieties are selected from linear and branched alkyl substituents, linear and branched alkenyl substituents, carbocyclic substituents, aryl substituents, aralkyl substituents, arylalkyl substituents, and alkylaryl substituents.
  • associative monomers can be prepared by the condensation (e.g., esterification or etherification) of a polyethoxylated and/or polypropoxylated aliphatic alcohol (typically containing a branched or unbranched C 8 -C 40 aliphatic moiety) with an ethylenically unsaturated monomer containing a carboxylic acid group (e.g., acrylic acid, methacrylic acid), an unsaturated cyclic anhydride monomer (e.g., maleic anhydride, itaconic anhydride, citraconic anhydride), a monoethylenically unsaturated monoisocyanate (e.g., ⁇ , ⁇ -dimethyl-m-isopropenyl benzyl isocyanate) or an ethylenically unsaturated monomer containing a hydroxyl group (e.g., vinyl alcohol, allyl alcohol).
  • Polyethoxylated and/or polypropoxylated aliphatic alcohols are ethylene oxide and/or propylene oxide adducts of a monoalcohol containing the C 8 -C 40 aliphatic moiety.
  • Alcohols containing a C 8 -C 40 aliphatic moiety are capryl alcohol, iso-octyl alcohol (2-ethyl hexanol), pelargonic alcohol (1-nonanol), decyl alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, cetearyl alcohol (mixture of C 16 -C 18 monoalcohols), stearyl alcohol, isostearyl alcohol, elaidyl alcohol, oleyl alcohol, arachidyl alcohol, behenyl alcohol, lignoceryl alcohol, ceryl alcohol, montanyl alcohol, melissyl, lacceryl alcohol, geddyl alcohol, and C 2 -C 20 alkyl substituted phenols (
  • HASE polymers are disclosed in U.S. Patent Nos. 3,657,175 ; 4,384,096 ; 4,464,524 ; 4,801,671 ; and 5,292,843 .
  • an extensive review of HASE polymers is found in Gregory D. Shay, Chapter 25, "Alkali-Swellable and Alkali-Soluble Thickener Technology A Review", Polymers in Aqueous Media - Performance Through Association, Advances in Chemistry Series 223, J. Edward Glass (ed.), ACS, pp. 457-494, Division Polymeric Materials, Washington, DC (1989 ).
  • Aculyn® 22 (INCI Name: Acrylates/Steareth-20 Methacrylate Copolymer), Aculyn® 44 (INCI Name: PEG-150/Decyl Alcohol/SMDI Copolymer), Aculyn 46® (INCI Name: PEG-150/Stearyl Alcohol/SMDI Copolymer), and Aculyn® 88 (INCI Name: Acrylates/Steareth-20 Methacrylate Crosspolymer) from Rohm & Haas, and NovethixTM L-10 (INCI Name: Acrylates/Beheneth-25 Methacrylate Copolymer) from Lubrizol Advanced Materials, Inc.
  • acid swellable associative polymers can be used with the hydrophobically modified, cationic polymers of the present invention.
  • Such polymers generally have cationic and associative characteristics.
  • These polymers are free radical addition polymers polymerized from a monomer mixture comprising an acid sensitive amino substituted hydrophilic monomer (e.g., dialkylamino alkyl (meth)acrylates or (meth)acrylamides), an associative monomer (defined hereinabove), a lower alkyl (meth)acrylate or other free radically polymerizable comonomers selected from hydroxyalkyl esters of (meth)acrylic acid, vinyl and/or allyl ethers of polyethylene glycol, vinyl and/or allyl ethers of polypropylene glycol, vinyl and/or allyl ethers of polyethylene glycol/polypropylene glycol, polyethylene glycol esters of (meth)acrylic acid, polypropylene glycol esters of (meth)acrylic
  • polymers can optionally be crosslinked.
  • acid sensitive is meant that the amino substituent becomes cationic at low pH values, typically ranging from 0.5 to 6.5.
  • Exemplary acid swellable associative polymers are commercially available under the trade name Structure® Plus (INCI Name: Acrylates/Aminoacrylates/C 10 -C 30 Alkyl PEG-20 Itaconate) from Akzo Nobel, and Carbopol® Aqua CC (INCI Name: Polyacrylates-1 Crosspolymer) from Lubrizol Advanced Materials, Inc.
  • the acid swellable polymer is a copolymer of one or more C 1 -C 5 alkyl esters of (meth)acrylic acid, C 1 -C 4 dialkylamino C 1 -C 6 alkyl methacrylate, PEG/PPG-30/5 allyl ether, PEG 20-25 C 10 -C 30 alkyl ether methacrylate, hydroxy C 2 -C 6 alkyl methacrylate crosslinked with ethylene glycol dimethacrylate.
  • Other useful acid swellable associative polymers are disclosed in U.S. Patent No. 7,378,479 .
  • Hydrophobically modified alkoxylated methyl glucosides such as, for example, PEG-120 Methyl Glucose Dioleate, PEG-120 Methyl Glucose Trioleate, and PEG-20 Methyl Glucose Sesquistearate, available from Lubrizol Advanced Materials, Inc., under the trade names, Glucamate® DOE-120, GlucamateTM LT, and GlucamateTM SSE-20, respectively, are also suitable as rheology modifiers.
  • Polysaccharides obtained from tree and shrub exudates such as gum Arabic, gum gahatti, and gum tragacanth, as well as pectin; seaweed extracts, such as alginates and carrageenans (e.g., lambda, kappa, iota, and salts thereof); algae extracts, such as agar; microbial polysaccharides, such as xanthan, gellan, and wellan; cellulose ethers, such as ethylhexylethylcellulose, hydroxybutylmethylcellulose, hydroxyethylmethylcellulose, hydroxypropylmethylcellulose, methylcellulose, carboxymethylcellulose, hydroxyethylcellulose, and hydroxypropylcellulose; polygalactomannans, such as fenugreek gum, cassia gum, locust bean gum, tara gum, and guar gum; starches, such as corn starch, tapioca starch, rice starch, wheat starch, potato starch and
  • the rheology modifier(s) can be used alone or in combination and may be present in the composition, on an actives basis, at a total concentration of 0.001-50 wt. %, e.g., at least 0.1 wt. %, or at least 1 wt. %, such as up to 20 wt. %, or up to 10 wt. %%, or up to 3 wt. %, based on the total weight of the composition.
  • composition may also include one or more surfactants, such as anionic, cationic, amphoteric, and nonionic surfactants, as well as mixtures thereof.
  • surfactants such as anionic, cationic, amphoteric, and nonionic surfactants, as well as mixtures thereof.
  • Cationic surfactants present may act as conditioning agents and assist in the heating step by ensuring that the heating device runs smoothly over the hair fibers. While the surfactants may also help to increase viscosity, they are not considered as rheology modifiers for purposes of describing the exemplary embodiment herein.
  • the cationic surfactants can be any of the cationic surfactants known or previously used in the art of aqueous surfactant compositions. Suitable classes of cationic surfactants are alkyl amines, alkyl imidaolines, ethoxylated amines, quaternary compounds, and quaternized esters. In addition, alkyl amine oxides can function as a cationic surfactant at a low pH.
  • Alkylamine surfactants can be salts of primary, secondary and tertiary fatty C 12 -C 22 alkylamines, substituted or unsubstituted, and substances sometimes referred to as "amidoamines".
  • alkylamines and salts thereof include dimethyl cocamine, dimethyl palmitamine, dioctylamine, dimethyl stearamine, dimethyl soyamine, soyamine, myristyl amine, tridecyl amine, ethyl stearylamine, N-tallowpropane diamine, ethoxylated stearylamine, dihydroxy ethyl stearylamine, arachidylbehenylamine, dimethyl lauramine, stearylamine hydrochloride, soyamine chloride, stearylamine formate, N-tallowpropane diamine dichloride, and amodimethicone (INCI name for a silicone polymer and blocked with amino functional groups, such as aminoeth
  • amidoamines and salts thereof include stearamido propyl dimethyl amine, stearamidopropyl dimethylamine citrate, palmitamidopropyl diethylamine, and cocamidopropyl dimethylamine lactate.
  • alkyl imidazoline surfactants include alkyl hydroxyethyl imidazoline, such as stearyl hydroxyethyl imidazoline, coco hydroxyethyl imidazoline, ethyl hydroxymethyl oleyl oxazoline, and the like.
  • ethyoxylated amines examples include PEG-cocopolyamine, PEG-15 tallow amine, quaternium-52, and the like.
  • R 5 R 6 R 7 R 8 N + ) E - wherein R 5 , R 6 , R 7 , and R 8 are independently selected from an aliphatic group having from 1 to about 22 carbon atoms, or an aromatic, alkoxy, polyoxyalkylene, alkylamido, hydroxyalkyl, aryl or alkylaryl group having 1 to about 22 carbon atoms in the alkyl chain; and E - is a salt-forming anion such as those selected from halogen, (e.g., chloride, bromide), acetate, citrate, lactate, glycolate, phosphate, nitrate, sulfate, and alkylsulfate.
  • halogen e.g., chloride, bromide
  • the aliphatic groups can contain, in addition to carbon and hydrogen atoms, ether linkages, ester linkages, and other groups such as amino groups.
  • the longer chain aliphatic groups e.g., those of about 12 carbons, or higher (C 10 -C 32 in the alkyl chain), can be saturated or unsaturated.
  • the aryl groups are selected from phenyl and benzyl.
  • Exemplary quaternary ammonium surfactants include, but are not limited to cetyl trimethylammonium chloride (cetrimonium chloride), cetylpyridinium chloride, dicetyl dimethyl ammonium chloride, dihexadecyl dimethyl ammonium chloride, stearyl dimethyl benzyl ammonium chloride, dioctadecyl dimethyl ammonium chloride, dieicosyl dimethyl ammonium chloride, didocosyl dimethyl ammonium chloride, dihexadecyl dimethyl ammonium chloride, dihexadecyl dimethyl ammonium acetate, behenyl trimethyl ammonium chloride (behentrimonium chloride), benzalkonium chloride, benzethonium chloride, and di(coconutalkyl) dimethyl ammonium chloride, ditallowdimethyl ammonium chloride, di(hydrogenated tallow) dimethyl ammonium chloride, di(hydrogenated
  • amine oxides can protonate and behave similarly to N-alkyl amines.
  • examples include, but are not limited to, dimethyl-dodecylamine oxide, oleyldi(2-hydroxyethyl) amine oxide, dimethyltetradecylamine oxide, di(2- hydroxyethyl)-tetradecylamine oxide, dimethylhexadecylamine oxide, behenamine oxide, cocamine oxide, decyltetradecylamine oxide, dihydroxyethyl C 12 - 15 alkoxypropylamine oxide, dihydroxyethyl cocamine oxide, dihydroxyethyl lauramine oxide, dihydroxyethyl stearamine oxide, dihydroxyethyl tallowamine oxide, hydrogenated palm kernel amine oxide, hydrogenated tallowamine oxide, hydroxyethyl hydroxypropyl C 12 -C 15 alkoxypropylamine oxide, lauramine oxide, myristamine oxide, cetylamine oxide,
  • Particularly useful cationic surfactants include fatty acid derivatives, such as fatty (C 10 -C 32 in the alkyl chain) alkylammonium chlorides, such as cetrimonium chloride and behentrimonium chloride. Such surfactants may also serve as conditioning agents and emollients.
  • surfactants may be present as various components, such as substantially insoluble materials requiring suspension or stabilization (e.g., a silicone, an oily material, a pearlescent material, aesthetic and cosmeceutical beads and particles, gaseous bubbles, exfoliants, and the like), may be present in the composition.
  • substantially insoluble materials requiring suspension or stabilization e.g., a silicone, an oily material, a pearlescent material, aesthetic and cosmeceutical beads and particles, gaseous bubbles, exfoliants, and the like
  • substantially insoluble materials requiring suspension or stabilization e.g., a silicone, an oily material, a pearlescent material, aesthetic and cosmeceutical beads and particles, gaseous bubbles, exfoliants, and the like
  • the anionic surfactant can be any of the anionic surfactants known or previously used in the art of aqueous surfactant compositions. Suitable anionic surfactants include but are not limited to alkyl sulfates, alkyl ether sulfates, alkyl sulphonates, alkaryl sulfonates, ⁇ -olefin-sulphonates, alkylamide sulphonates, alkarylpolyether sulphates, alkylamidoether sulphates, alkyl monoglyceryl ether sulfates, alkyl monoglyceride sulfates, alkyl monoglyceride sulfonates, alkyl succinates, alkyl sulfosuccinates, alkyl sulfosuccinamates, alkyl ether sulphosuccinates, alkyl amidosulfosuccinates; alkyl sulphoacetates, alkyl phosphate
  • the cation moiety of the forgoing salts is selected from sodium, potassium, magnesium, ammonium, mono-, di- and triethanolamine salts, and mono-, di-, and tri-isopropylamine salts.
  • the alkyl and acyl groups of the foregoing surfactants contain from about 6 to about 24 carbon atoms in one aspect, from 8 to 22 carbon atoms in another aspect and from about 12 to 18 carbon atoms in a further aspect and may be unsaturated.
  • the aryl groups in the surfactants are selected from phenyl or benzyl.
  • the ether containing surfactants set forth above can contain from 1 to 10 ethylene oxide and/or propylene oxide units per surfactant molecule in one aspect, and from 1 to 3 ethylene oxide units per surfactant molecule in another aspect.
  • Suitable anionic surfactants include sodium, potassium, lithium, magnesium, and ammonium salts of laureth sulfate, trideceth sulfate, myreth sulfate, C 12 -C 13 pareth sulfate, C 12 -C 14 pareth sulfate, and C 12 -C 15 pareth sulfate, ethoxylated with 1, 2, and 3 moles of ethylene oxide; sodium, potassium, lithium, magnesium, ammonium, and triethanolamine lauryl sulfate, coco sulfate, tridecyl sulfate, myrstyl sulfate, cetyl sulfate, cetearyl sulfate, stearyl sulfate, oleyl sulfate, and tallow sulfate, disodium lauryl sulfosuccinate, disodium laureth sulfosuccinate, sodium cocoyl isethionat
  • Amphoteric or zwitterionic surfactants are molecules that contain acidic and basic moieties and have the capacity of behaving either as an acid or a base.
  • Suitable surfactants can be any of the amphoteric surfactants known or previously used in the art of aqueous surfactant compositions.
  • Exemplary amphoteric surfactant classes include but are not limited to amino acids (e.g., N-alkyl amino acids and N-acyl amino acids), betaines, sultaines, and alkyl amphocarboxylates.
  • Amino acid based surfactants suitable herein include surfactants represented by the formula: wherein R 10 represents a saturated or unsaturated hydrocarbon group having 10 to 22 carbon atoms or an acyl group containing a saturated or unsaturated hydrocarbon group having 9 to 22 carbon atoms, Y is hydrogen or methyl, Z is selected from hydrogen, -CH 3 , -CH(CH 3 ) 2 , -CH 2 CH(CH 3 ) 2 , -CH(CH 3 )CH 2 CH 3 , -CH 2 C 6 H 5 , -CH 2 C 6 H 4 OH, -CH 2 OH, -CH(OH)CH 3 , -(CH 2 ) 4 NH 2 , -(CH 2 ) 3 NHC(NH)NH 2 , -CH 2 C(O)O - M + , -(CH 2 ) 2 C(O)O - M + .
  • M is a salt forming cation.
  • R 10 represents a radical selected from a linear or branched C 10 to C 22 alkyl group, a linear or branched C 10 to C 22 alkenyl group, an acyl group represented by R 11 C(O)-, wherein R 11 is selected from a linear or branched C 9 to C 22 alkyl group, a linear or branched C 9 to C 22 alkenyl group.
  • M + is selected from sodium, potassium, ammonium, and triethanolamine (TEA).
  • the amino acid surfactants can be derived from the alkylation and acylation of ⁇ -amino acids such as, for example, alanine, arginine, aspartic acid, glutamic acid, glycine, isoleucine, leucine, lysine, phenylalanine, serine, tyrosine, and valine.
  • ⁇ -amino acids such as, for example, alanine, arginine, aspartic acid, glutamic acid, glycine, isoleucine, leucine, lysine, phenylalanine, serine, tyrosine, and valine.
  • N-acyl amino acid surfactants are, but not limited to the mono- and di- carboxylate salts (e.g., sodium, potassium, ammonium and TEA) of N-acylated glutamic acid, for example, sodium cocoyl glutamate, sodium lauroyl glutamate, sodium myristoyl glutamate, sodium palmitoyl glutamate, sodium stearoyl glutamate, disodium cocoyl glutamate, disodium stearoyl glutamate, potassium cocoyl glutamate, potassium lauroyl glutamate, and potassium myristoyl glutamate; the carboxylate salts (e.g., sodium, potassium, ammonium and TEA) of N-acylated alanine, for example, sodium cocoyl alaninate, and TEA lauroyl alaninate; the carboxylate salts (e.g., sodium, potassium, ammonium and TEA) of N-acylated glycine, for example, sodium cocoy
  • the betaines and sultaines useful in the composition are selected from alkyl betaines, alkylamino betaines, and alkylamido betaines, as well as the corresponding sulfobetaines (sultaines) represented by the formulas: wherein R 12 is a C 7 -C 22 alkyl or alkenyl group, each R 13 independently is a C 1 -C 4 alkyl group, R 14 is a C 1 -C 5 alkylene group or a hydroxy substituted C 1 -C 5 alkylene group, n is an integer from 2 to 6, A is a carboxylate or sulfonate group, and M is a salt forming cation.
  • R 12 is a C 11 -C 18 alkyl group or a C 11 -C 18 alkenyl group.
  • R 13 is methyl.
  • R 14 is methylene, ethylene or hydroxy propylene.
  • n is 3.
  • M is selected from sodium, potassium, magnesium, ammonium, and mono-, di- and triethanolamine cations.
  • betaines examples include lauryl betaine, coco betaine, oleyl betaine, cocohexadecyl dimethylbetaine, lauryl amidopropyl betaine, cocoamidopropyl betaine, and cocamidopropyl hydroxysultaine.
  • alkylamphocarboxylates such as the alkylamphoacetates and alkylamphopropionates (mono- and disubstituted carboxylates) can be represented by the formula: wherein R 12 is a C 7 -C 22 alkyl or alkenyl group, R 15 is -CH 2 C(O)O - M + , -CH 2 CH 2 C(O)O - M + , or -CH 2 CH(OH)CH 2 SO 3 - M + , R 16 is a hydrogen or -CH 2 C(O)O - M + , and M is a cation selected from sodium, potassium, magnesium, ammonium, and mono-, di- and triethanolamine.
  • Exemplary alkylamphocarboxylates include sodium cocoamphoacetate, sodium lauroamphoacetate, sodium capryloamphoacetate, disodium cocoamphodiacetate, disodium lauroamphodiacetate, disodium caprylamphodiacetate, disodium capryloamphodiacetate, disodium cocoamphodipropionate, disodium lauroamphodipropionate, disodium caprylamphodipropionate, and disodium capryloamphodipropionate.
  • the nonionic surfactant can be any of the nonionic surfactants known or previously used in the art of aqueous surfactant compositions.
  • Suitable nonionic surfactants include, but are not limited to, aliphatic (C 6 -C 18 ) primary or secondary linear or branched chain acids, alcohols or phenols; alkyl ethoxylates; alkyl phenol alkoxylates (especially ethoxylates and mixed ethoxy/propoxy moieties); block alkylene oxide condensates of alkyl phenols; alkylene oxide condensates of alkanols; and ethylene oxide/propylene oxide block copolymers.
  • nonionic surfactants include mono- or dialkyl alkanolamides; alkyl polyglucosides (APGs); sorbitan fatty acid esters; polyoxyethylene sorbitan fatty acid esters; polyoxyethylene sorbitol esters; polyoxyethylene acids, and polyoxyethylene alcohols.
  • nonionic surfactants include coco mono- or diethanolamide, coco glucoside, decyl diglucoside, lauryl diglucoside, coco diglucoside, polysorbate 20, 40, 60, and 80, ethoxylated linear alcohols, cetearyl alcohol, lanolin alcohol, stearic acid, glyceryl stearate, PEG-100 stearate, laureth 7, and oleth 20.
  • non-ionic surfactants include alkoxylated methyl glucosides such as, for example, methyl gluceth-10, methyl gluceth-20, PPG-10 methyl glucose ether, and PPG-20 methyl glucose ether, available from Lubrizol Advanced Materials, Inc., under the trade names, Glucam® E10, Glucam® E20, Glucam® P10, and Glucam® P20, respectively; and hydrophobically modified alkoxylated methyl glucosides, such as PEG 120 methyl glucose dioleate, PEG-120 methyl glucose trioleate, and PEG-20 methyl glucose sesquistearate, available from Lubrizol Advanced Materials, Inc., under the trade names, Glucamate® DOE-120, GlucamateTM LT, and GlucamateTM SSE-20, respectively, are also suitable.
  • Other exemplary hydrophobically modified alkoxylated methyl glucosides are disclosed in U.S. Patent Nos. 6,573,375 and 6,7
  • surfactants which can be utilized in the composition are set forth in more detail in WO 99/21530 , U.S. Patent Nos. 3,929,678 , 4,565,647 , 5,720,964 , and 5,858,948 .
  • suitable surfactants are also described in McCutcheon's Emulsifiers and Detergents (North American and International Editions, by Schwartz, Perry and Berch ).
  • the amounts of the surfactant utilized in a composition comprising the exemplary thermally-activated agent can vary widely depending on a desired application, the amounts which are often utilized generally range from 1 wt. % to 80 wt. %, on an actives basis.
  • the surfactant may be present in the composition, on an actives basis, at a total concentration of 0.001-20 wt. %, e.g., at least 0.1 wt. %.
  • Fatty alcohols and fatty acids, as well as their alkoxylates, the partial esters of polyglycerols, as well as the organosiloxanes are useful herein.
  • the fatty alcohol may be obtained from natural sources and thus be a mixture of alcohols.
  • Emulsifiers when employed in the exemplary compositions, may include fatty alcohols, such as or C 12 -C 32 or C 12 -C 22 fatty alcohols, alkoxylated alcohols, such as C 12 -C 32 or C 12 -C 22 alkoxylated alcohols, fatty acids, such as C 12 -C 32 or C 12 -C 22 fatty acids, alkoxylated fatty acids, such as C 12 -C 32 or C 12 -C 22 alkoxylated fatty acids (the alkoxylates each having 10 to 80 units of ethylene oxide, propylene oxide, and combinations of ethylene oxide/propylene oxide present in the molecule), C 8 -C 22 alkyl polyglycosides (APGs), ethoxylated sterols (wherein the number of ethylene oxide units ranges from 2 to about 150), partial esters of polyglycerols, esters and partial esters of polyols having 2 to 6 carbon atoms, partial esters of polygly
  • cetearyl alcohol which is a mixture of fatty alcohols, predominantly cetyl and stearyl alcohols. Since such fatty alcohols can serve as a rheology modifier in the composition, they are thus considered as rheology modifiers for purposes of defining the weights of components of the composition. Such fatty alcohols may also serve as emollients and/or conditioning agents.
  • Particularly suitable emulsifiers include polyoxyethylene ethers, such as ceteareth-n (where n represents the number of polyethylene units in the chain, such as from 2-100, e.g., 5-50), such as ceteareth 20.
  • polyoxyethylene ethers such as ceteareth-n (where n represents the number of polyethylene units in the chain, such as from 2-100, e.g., 5-50), such as ceteareth 20.
  • Exemplary alkyl glucosides and oligoglycosides can be selected from octyl glucoside, decyl glucoside, lauryl glucoside, palmityl glucoside, isostearyl glucoside, stearyl glucoside, arachidyl glucoside and behenyl glucoside, and mixtures thereof.
  • Emulsifiers based on the esters and partial esters of polyols having 2 to 6 carbon atoms that are condensed with linear saturated and unsaturated fatty acids having 12 to 30 carbon atoms are, for example, the monoesters and diesters of glycerol or ethylene glycol or the monoesters of propylene glycol with saturated and unsaturated C 12 -C 30 fatty acids.
  • the emulsifier may be suitably present at 0.01-20 wt. % of the composition, such as at least 0.1 wt. %, e.g., up to 5 wt. %, which for purposes of computing amounts present in the composition, excludes those listed above as rheology modifiers.
  • conditioning agents include polyquaternium-n (polycationic polymers including a quaternary ammonium center in the polymer), wherein n is from 1-47, each n designating a specific polymer, such as polyquaternium 37, and amine-functionalized silicones, such as amodimethicone.
  • Another suitable conditioning agent is hydrolyzed keratin.
  • Such conditioning agents may be present at from 0.01-20 wt. % of the composition, such as at least 0.1 wt. %, e.g., up to 5 wt. %.
  • Humectants suitable for use in the composition of the invention include, but are not limited to, glycerol, polyglycerols, sorbitol, propane-1,2-diol (propylene glycol), butane-1,2,3-triol, polyethylene glycols, glucose, mannitol, xyliyol, and mixtures thereof.
  • Such humectants may be present at from 0.01-20 wt. % of the composition, such as at least 0.1 wt. %, or at least 1 wt. %, e.g., up to 8 wt. %, or up to 5 wt. %.
  • any preservative suitable for use in personal care can be used in the composition for straightening hair.
  • Suitable preservatives include polymethoxy bicyclic oxazolidine, methyl paraben, propyl paraben, ethyl paraben, butyl paraben, benzyltriazole, DMDM hydantoin (also known as 1,3-dimethyl-5,5-dimethyl hydantoin), imidazolidinyl urea, phenoxyethanol, phenoxyethylparaben, methylisothiazolinone, methylchloroisothiazolinone, benzoisothiazolinone, triclosan, and suitable polyquaternium compounds as disclosed above (e.g., Polyquaternium-1).
  • acid based preservatives are useful in the exemplary compositions.
  • the use of acid based preservatives facilitates the formulation of products in the low pH range. Lowering the pH of a formulation inherently provides an inhospitable environment for microbial growth in addition to being suited to the straightening process.
  • formulating at low pH enhances the efficacy of acid based preservatives, and affords a personal care product which maintains an acidic pH balance on the skin. Any acid based preservative that is useful in personal care products can be used in the exemplary compositions.
  • the acid preservative is a carboxylic acid compound represented by the formula: R 3 C(O)OH, wherein R 3 represents hydrogen, a saturated and unsaturated hydrocarbyl group containing 1 to 8 carbon atoms or C 6 to C 10 aryl.
  • R 3 is selected from a hydrogen, a C 1 to C 8 alkyl group, a C 2 to C 8 alkenyl group, or phenyl.
  • Exemplary acids are, but are not limited to, formic acid, acetic acid, propionic acid, sorbic acid, caprylic acid, and benzoic acid, and mixtures thereof.
  • suitable acids include but are not limited to, oxalic acid, succinic acid, glutaric acid, adipic acid, azelaic acid, maleic acid, fumaric acid, lactic acid, glyceric acid, tartronic acid malic acid, tartaric acid, gluconic acid, citric acid, ascorbic acid, salicylic acid, phthalic acid, mandelic acid, benzilic acid, and mixtures thereof.
  • Salts of the foregoing acids are also useful as long as they retain efficacy at low pH values.
  • Suitable salts include the alkali metal (e.g., sodium, potassium, calcium) and ammonium salts of the acids enumerated above.
  • the acid based preservatives and/or their salts can be used alone or in combination with non-acidic preservatives typically employed in personal care, home care, health care, and institutional and industrial care products.
  • the preservatives may comprise from 0.01 wt.% to 3.0 wt.% in one aspect, or from 0.1 wt.% to 1 wt.%, or from 0.3 wt.% to 1 wt.%, of the total weight of the hair straightening composition.
  • Chelating agents can be employed to stabilize the composition against the deleterious effects of metal ions.
  • suitable chelating agents include EDTA (ethylene diamine tetraacetic acid) and salts thereof such as disodium EDTA, citric acid and salts thereof, cyclodextrins, and the like, and mixtures thereof.
  • Such suitable chelating agents can comprise 0.001 wt. % to 3 wt. %, such as 0.01 wt. % to 2 wt. %, or 0.01 wt. % to 1 wt. % of the total weight of the hair straightening composition.
  • any known aerosol propellant can be utilized to deliver the hair straightening compositions onto the surface of the hair to be straightened.
  • exemplary propellants include lower boiling hydrocarbons such as C 3 -C 6 straight and branched chain hydrocarbons.
  • exemplary hydrocarbon propellants include propane, butane, isobutene, and mixtures thereof.
  • Other suitable propellants include ethers, such as, dimethyl ether, hydrofluorocarbons, such as, 1,1-difluoroethane, and compressed gases, such as air and carbon dioxide.
  • these compositions can contain from 0.1 wt. % to 60 wt. %, or 0.5 to 35 wt. % propellant, based on the total weight of the composition.
  • Fragrance and perfume components that may be used in the exemplary composition include natural and synthetic fragrances, perfumes, scents, and essences and any other substances which emit a fragrance.
  • natural fragrances there are those of vegetable origin, such as oil extracts from flowers (e.g., lily, lavender, rose, jasmine, neroli, ylang-ylang), stems and leaves (geranium, patchouli, petitgrain, peppermint), fruits (aniseed, coriander, fennel, needle juniper), fruit skin (bergamot, lemon, orange), roots (mace, angelica, celery, cardamom, costus, iris, sweet flag), woods (pine tree, sandalwood, guaiacum wood, cedar, rosewood, cinnamon), herbs and grasses (tarragon, lemongrass, sage, thyme), needles and twigs (spruce, pine, European red pine, stone pine), and resins and balsam (galbanum, elemi, be
  • fragrances and perfumes are the aromatic esters, ethers, aldehydes, ketones, alcohols, and hydrocarbons including benzyl acetate, phenoxyethyl isobutylate, p-tert-butylcyclohexyl acetate, linalyl acetate, dimethylbenzylcarbinyl acetate, phenylethyl acetate, linalyl benzoate, benzyl formate, ethylmethylphenyl glycinate, allylcyclohexyl propionate, styralyl propionate, and benzyl salicylate; benzylethyl ether; straight chain alkanals having 8 to 18 carbon atoms, citral, citronellal, citronellyloxyaldehyde, cyclamen aldehyde, hydroxycitronellal, lilial, and bougeonal; ionone compounds, ⁇ -isomethyl
  • Suitable botanical agents useful herein may include, for example, extracts from Echinacea (e.g., sp. angustifolia, purpurea, pallida), yucca glauca, willow herb, basil leaves, Vietnamese oregano, carrot root, grapefruit, fennel seed, rosemary, tumeric, thyme, blueberry, bell pepper, blackberry, spirulina, black currant fruit, tea leaves, such as for, example, Chinese tea, black tea (e.g., var. Flowery Orange Pekoe, Golden Flowery Orange Pekoe, Fine Tippy Golden Flowery Orange Pekoe), green tea (e.g., var.
  • Botanical extracts may also include, for example, chlorogenic acid, glutathione, glycrrhizin, neohesperidin, quercetin, rutin, morin, myricetin, absinthe, and chamomile.
  • Hair fixing agents may be included in addition to the exemplary thermally-activated agent, including polymer fixatives such as 3-aminopropyl methyl, dimethyl, reaction products of silicones and siloxanes with 2-ethyl-4,5-dihydrooxazole homopolymer, ethyl sulfates, such as Polysilicone-9, and film-forming polymers such as polyacrylic acid and sodium polyacrylate polymer fixatives, such as FixateTM RSP available from Lubrizol Corp.
  • polymer fixatives such as 3-aminopropyl methyl, dimethyl, reaction products of silicones and siloxanes with 2-ethyl-4,5-dihydrooxazole homopolymer, ethyl sulfates, such as Polysilicone-9
  • film-forming polymers such as polyacrylic acid and sodium polyacrylate polymer fixatives, such as FixateTM RSP available from Lubrizol Corp.
  • the hair fixing agent may be present in the composition at from 0.001 wt. % to 20 wt. %, such as at least 0.1 wt. %, or up to 5 wt. %.
  • Emollients may include silicone oils, functionalized silicone oils, hydrocarbon oils, fatty alcohols, fatty alcohol ethers, fatty acids, esters of monobasic and/or dibasic and/or tribasic and/or polybasic carboxylic acids with mono and polyhydric alcohols, polyoxyethylenes, polyoxypropylenes, mixtures of polyoxyethylene and polyoxypropylene ethers of fatty alcohols, and mixtures thereof.
  • the emollients may be either saturated or unsaturated, have an aliphatic character and be straight or branched chained or contain alicyclic or aromatic rings.
  • An example emollient useful herein is diisopropyl adipate.
  • Buffering agents can be used in the exemplary compositions.
  • Suitable buffering agents include alkali or alkali earth metal carbonates, phosphates, bicarbonates, citrates, borates, acetates, acid anhydrides, succinates, and the like, such as sodium phosphate, sodium citrate, sodium acetate, sodium bicarbonate, and sodium carbonate.
  • auxilliary components useful herein may include UV-absorbers, such as benzophenone-4.
  • composition may exclude certain components, such as hair coloring agents (hair dyes), peptides, sulfites, bisulfites, and cyclic mercapto compounds which are not of benefit in simply a hair-straightening application.
  • hair coloring agents hair dyes
  • peptides peptides
  • sulfites peptides
  • bisulfites cyclic mercapto compounds
  • cream formulations may be formulated as shown in Table 1: Table 1: Example Compositions Component Example 1 Wt. % actives Example 2 Wt. % actives Thermally-activated agent 5-95, or 5-60 15-50 Rheology modifier 0-20 1-10 Cationic surfactant 0-20 1-5 pH modifier (or in an amount sufficient to provide a pH of up to 8.5) 0.01-10 0.02-5 Preservative 0-2 0.01-1 Organic solvent 0-50 0.2-30 Other components 0-20 0-10 Water q.s. to 100% q.s. to 100%
  • compositions can be formed by combining ranges from Examples 1 and 2. Additionally, the selected process, such as contact time and heating temperature, may also influence the selection of the composition components and their amounts, as demonstrated by the examples below.
  • the semi-permanent hair straightening composition can be provided and dispensed from suitable package forms, such as pressurized and non-pressurized containers, such as cans, bottles, packets, ampoules, jars, tubes, and the like.
  • Spray compositions can be dispensed from finger-actuated pump devices, either as pressurized aerosol sprays, mousses, spritzes, and foams containing propellant, or as non-pressurized, mechanically propelled sprays and foams.
  • the exemplary composition can be utilized on hair to impart an excellent straightening effect by using heat.
  • the treatment method includes first coating the hair with the composition. This may be performed with any suitable applicator, such as a brush, comb, sponge, pad, cloth, fingers e.g., while wearing gloves, to coat the fibers with the composition.
  • the composition is left in contact with the hair for a sufficient time period for the thermally-activated agent to penetrate into the fibers, such as several minutes, e.g., at least five or at least ten minutes, or at least twenty minutes, or at least thirty minutes, and up to sixty, or up to forty, or up to thirty minutes.
  • the optimum contacting time may vary, depending on factors such as the concentration of thermally-activated agent and the temperature of the heating device used to contact the hair in the heating stage.
  • the heat is applied with the heating device which provides a temperature sufficient to activate the thermally-activated agent of Structure (1), i.e. a temperature of at least 200°C, or at least 205°C or at least or 210°C and up to 230°C or up to 225°C, or up to 220°C.
  • the heating device is retained in contact with the hair for sufficient time to effect the desired modification, such as an increase in length of a hair tress of at least 5%, or at least 10%.
  • the time depends on a number of factors such as the moisture content of the hair, temperature of the heating device, concentration of the thermally-activated agent and so forth, but is generally at least 10 seconds, or at least 1 or 2 minutes, in total, for each centimeter length of hair.
  • the heating device is a flat iron.
  • the heating device has at least one surface (which is brought into contact with the fibers) which is raised, e.g., with an electric power source, to a surface temperature of at least 200°C, or at least 205°C or at least or 210°C and up to 230°C or up to 225°C, or up to 220°C.
  • the temperature of the hair tress can be measured, for example, with a thermocouple positioned within the hair tress and may reach a temperature of at least 150°C or at least 170°C during the heating with the heating device.
  • the hair can be dried to some extent after treatment with the straightening composition and prior to application of heat to raise the temperature of the keratin fibers and/or to avoid substantial release of steam during the heating stage.
  • partial drying may be achieved by blow drying with a hairdryer, a drying hood at a temperature of 100°C, by free drying, wiping with a towel, etc.
  • the moisture content of the composition may be reduced to 10 wt. % or less, such as 2 wt. %, prior to applying heat with the heating device.
  • the drying is performed to remove solvent while retaining at least a portion, or all, of the applied thermally-activated agent on the hair. For this reason also, the hair is not rinsed (e.g., with water or other aqueous solution) between the applying and the heating stages in the exemplary embodiment.
  • the end of the iron that comes into contact with the hair generally has two flat surfaces. These two flat surfaces may be metallic or ceramic. They may be smooth or notched.
  • the application of the iron may be performed by successive touches separated by a few seconds, or by gradual moving or sliding along locks, etc.
  • the application of the iron in the exemplary process is performed by continuous movement from the root to the end, in one or more passes, such as at least five passes.
  • the hot flat iron softens hard ⁇ -keratins and straightens the hair fiber and synergistically, the heat imparted by the flat iron activates a reaction (e.g., a cross-linking or other modification reaction) between the cyclic carbonates and the amine groups of the hair fibers, possibly resulting in N, N'- disubstituted urea linkages. This results in a fixation of the newly formed shape.
  • a reaction e.g., a cross-linking or other modification reaction
  • Alkylene carbonates in particular, according to the present invention, ethylene carbonate
  • ethylene carbonate have been shown to be effective protein modifier or cross-linking agents imparting the ease and effectiveness of desired reactions acting upon keratin peptides.
  • applying an aqueous solution containing ethylene carbonate to hair followed by a hot flat iron treatment e.g., at ⁇ 210°C
  • the process provides some or all of the following attributes:
  • the hair type and curliness is based on the definition published by L'Oréal ( Roland de la Mettrie, et al. "Shape Variability and Classification of Human Hair: A Worldwide Approach," Human Biology, Jun 2007 ).
  • the samples used herein were curly, classed as type 4-5.
  • the hair-tress typically becomes type I.
  • the hair relaxes on washing. If, after 3-shampoo-wash-cycle, the hair-tress relaxes to type 3-4, this can be considered as inefficiently straightened (relaxed).
  • curly Brazilian hair tresses were obtained from International Hair Importer and Product Inc. Each single hair-tress is about 2.5g in weight and has approximate dimensions of 20cm in length and 10 cm in width at the widest point. The tresses are each clamped at the root end.
  • each virgin dark brown curly hair-tress was shampooed by using a commercial clarifying shampoo (VO5TM or Suave TM shampoo) by gently massaging for 30 seconds followed by rinsing for 60 seconds with running warm water (35-38°C). Each washed hair-tress is then dried at room temperature under 30-50 %RH conditions.
  • VO5TM or Suave TM shampoo commercial clarifying shampoo
  • This method is used primarily to screen and select candidate molecules as possible thermally-activated agents.
  • a solution of the candidate molecule is prepared in a suitable solvent system.
  • the hair-tress is immersed completely in the solution with controlled concentration of candidate thermally-activated agent, pH, temperature and soaking time, such as for up to 60 minutes. Then, the hair-tress is removed from the solution, excess amount of material squeezed out, and the tress is blow-dried to at least 95% dryness before thermal straightening.
  • thermally-activated agents which perform well on the solution dip method are incorporated in a cationic emulsion or cream chassis system at different levels and pH, as shown in Table 2: Table2: Cream Chassis Formulas Component Function Amount of active, wt. % thermally-activated agent, e.g., EC Thermally-activated hair straightening agent Different amounts Paraffinum Liquidum Rheology modifier and emollient 3.00 Cetearyl alcohol Rheology modifier and conditioning agent 2.50 Diisopropyl adipate Emollient 1.50 Cetrimonium chloride (50 wt. % active) Surfactant/Conditioning agent 1.40 Ceteareth-20 Emulsifier Different amounts Citric acid (10 wt.
  • the product is applied on a cleaned curly hair-tress and allowed to rest according to the protocol. After the controlled application time, the hair-tress is blow-dried to at least 95% of dryness before thermal straightening.
  • the hair-tress is allowed to cool down to the room temperature.
  • the shampoo-wash-fastness is carried out by applying shampoo (VO5 or Suave shampoo) on the hair-tress which is massaged for 30 seconds followed by rinsing for 60 seconds with running warm water (32 - 35°C). The washed hair-tress is then dried at 23°C and 50% RH. Consecutive shampoo-wash-cycles are carried out without the drying step.
  • Humidity Resistance Thermal-straightened hair-tresses after a certain numbers of shampoo-wash are dried before being placed in a humidity chamber with controlled temperature and %RH.
  • the examination of thermally straightened hair-tresses is performed by visually examining a tress which has been treated in a solution containing up to 30 wt. % of a candidate thermally-activated agent for 45 minutes, flat-ironed at 210°C (10 x 12 seconds). After three consecutive wash cycles, if the dried hair-tress (23°C and 50% RH) becomes curly, this material is considered not effective, i.e. not worth a further evaluation in a cream formulation.
  • Thermal Breakage Quantification Thermal straightened hair-tresses after a certain number of shampoo-washes are dried before being placed in the humidity chamber with controlled temperature and %RH. Then a single hair-tress is combed with a comb with a constant force from the root to the tip, and the stroke is repeated for 100 times. When completed, hair fiber fragments that have broken from the tress are counted for comparison.
  • Tables 3-5 show some of the results obtained for the cream formulations where the following abbreviations are used:
  • Examples 21-27 and 32-36 had almost no malodor, and were smooth, sleek and healthy looking.
  • thermally straightening efficiency of exemplary thermally-activated agents (ethylene carbonate, trimethylene carbonate, and oxazolidinone) and other small molecules, such as formaldehyde, urea, and glyoxylic acid.
  • exemplary thermally-activated agents ethylene carbonate, trimethylene carbonate, and oxazolidinone
  • other small molecules such as formaldehyde, urea, and glyoxylic acid.
  • a curly hair-tress was completely immersed in an aqueous solution of a selected one of the small molecules and soaked for 45 minutes. Each solution contained an equimolar amount of the selected small molecule. The hair-tress was then removed from the solution, excess water was squeezed out manually, and the hair dried by a blower dryer to the desired dryness before thermal straightening, as described above.
  • the imaging analysis method was used to measure the total length and width of the hair-tress before and after the thermal straightening process, and after each shampoo-wash-cycle. More specifically, photographs of hair tresses or bundles of hair tresses were taken against a solid color background with a tripod-mounted digital camera. Illumination was selected to minimize shadows which could affect measurements.
  • the tress was hung from a spindle that enabled the tress to be rotated 90 degrees so that pictures could be taken from four different angles, providing a full view of the tress, with a ruler mounted close to the tress as a scale.
  • the National Institutes for Health's Image J software program was used for image processing and analysis. Table 6 shows the length, and width (at half-length).
  • the curly hair-tress has a contour length of 20cm, and the top glued part is 2.0cm wide and is about 0.4cm of length. Therefore, the effective hair-tress contour length is 19.6cm.
  • ethylene carbonate (EC) and trimethylene carbonate (TC) behave similarly to formaldehyde (F) and glyoxylic acid (GA), yet without the potential hazards that these small molecules pose.
  • Oxazolidinone (O) gives better straightening results than urea (U) and ethylene urea (EU). Urea and ethylene urea relax the curly hair-tress to some degree.
  • the ranking of the molecules for semi-permanent thermal straightening efficiency from this data is: GA ⁇ EC ⁇ F ⁇ TC > O > EU > U Table 6: Thermal straightening efficacy analyzed by imaging analysis method Small Molecule U EU O TC F EC GA Length max (cm) Control 15.9 16.0 16.1 16.5 16.0 16.8 16.1 Thermally-treated 19.6 19.4 19.3 19.8 19.4 19.4 19.5 Av.:1-24 shampoos 18.2 ⁇ 0. 2 18.2 ⁇ 0. 2 18.4 ⁇ 0. 1 19.0 ⁇ 0. 1 19.1 ⁇ 0.1 19.4 ⁇ 0.1 19.2 ⁇ 0.
  • ethylene carbonate or trimethylene carbonate was admixed with various commercial hair treatment products and the mixtures were evaluated for straightening efficiency.
  • the ethylene carbonate or trimethylene carbonate was melted at about 40°C and the resulting liquid was quickly added to the selected commercial product and mixed until homogenous.
  • the EC or TC active level of the mixture was 15 wt. % - 30 wt. %.
  • Table 8 shows an example spray formulation.
  • Table 9 shows an example cream formulation.
  • Table 10 shows another example formulation.
  • Table 11 shows another example formulation.
  • Table 12 shows an example gel formulation.
  • each chemical or composition referred to herein should be interpreted as being a commercial grade material which may contain the isomers, by-products, derivatives, and other such materials which are normally understood to be present in the commercial grade. However, the amount of each chemical component is presented exclusive of any solvent or diluent oil, which may be customarily present in the commercial material, unless otherwise indicated.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)
  • Dermatology (AREA)
EP14705651.9A 2013-02-06 2014-02-03 Semi-permanent hair straightening composition and method Active EP2953610B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201361761326P 2013-02-06 2013-02-06
PCT/US2014/014409 WO2014123805A1 (en) 2013-02-06 2014-02-03 Semi-permanent hair straightening composition and method

Publications (2)

Publication Number Publication Date
EP2953610A1 EP2953610A1 (en) 2015-12-16
EP2953610B1 true EP2953610B1 (en) 2019-04-10

Family

ID=50150808

Family Applications (1)

Application Number Title Priority Date Filing Date
EP14705651.9A Active EP2953610B1 (en) 2013-02-06 2014-02-03 Semi-permanent hair straightening composition and method

Country Status (10)

Country Link
US (1) US9872824B2 (enrdf_load_stackoverflow)
EP (1) EP2953610B1 (enrdf_load_stackoverflow)
JP (1) JP6452625B2 (enrdf_load_stackoverflow)
KR (1) KR102197099B1 (enrdf_load_stackoverflow)
CN (1) CN105073090B (enrdf_load_stackoverflow)
AU (1) AU2014215569B2 (enrdf_load_stackoverflow)
BR (1) BR112015018706B1 (enrdf_load_stackoverflow)
CA (1) CA2899597A1 (enrdf_load_stackoverflow)
MX (1) MX357773B (enrdf_load_stackoverflow)
WO (1) WO2014123805A1 (enrdf_load_stackoverflow)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022182596A1 (en) 2021-02-23 2022-09-01 Angus Chemical Company Substitution of ammonia in hair altering products

Families Citing this family (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6395836B2 (ja) * 2013-08-13 2018-09-26 ロレアル 有機一酸及びセルロースポリマーを含む組成物を用いて毛髪を処置する方法
EP2857004B1 (en) 2013-10-07 2018-07-04 The Procter and Gamble Company Hair straightening method involving reducing sugars
MX2016008163A (es) 2013-12-19 2016-09-16 Procter & Gamble Formacion de fibras de queratina mediante el uso de una composicion reductora y una composicion fijadora.
CN105828791B (zh) 2013-12-19 2019-09-20 宝洁公司 使用碳酸酯使角蛋白纤维成形
JP6346951B2 (ja) 2013-12-19 2018-06-20 ザ プロクター アンド ギャンブル カンパニー ケラチン繊維の成形方法
MX361100B (es) 2013-12-19 2018-11-27 Procter & Gamble Modelado de fibras de queratina mediante el uso de un azucar.
EP3082736B1 (en) 2013-12-19 2018-08-08 The Procter and Gamble Company Shaping keratin fibres using 2-hydroxypropane-1,2,3-tricarboxylic acid and/or 1,2,3,4-butanetetracarboxylic acid
US9918921B2 (en) 2013-12-19 2018-03-20 The Procter & Gamble Company Methods for shaping fibrous material and treatment compositions therefor
EP3082735B1 (en) 2013-12-19 2018-05-02 The Procter and Gamble Company Shaping keratin fibres using oxoethanoic acid and/or derivatives thereof
MX2016007779A (es) 2013-12-19 2016-09-07 Procter & Gamble Formacion de fibras de queratina mediante el uso de ester de carbonato.
WO2015094759A1 (en) 2013-12-19 2015-06-25 The Procter & Gamble Company Shaping keratin fibres using an active agent comprising at least two functional groups selected from: -c(oh)- and -c(=o)oh
EP3297730A1 (en) * 2014-12-19 2018-03-28 The Procter and Gamble Company Method of shaping keratin fibres
EP3256096B1 (en) 2014-12-19 2019-04-17 The Procter and Gamble Company Shaping keratin fibres using arabinose and ethylene carbonate
CN107106472A (zh) * 2014-12-19 2017-08-29 宝洁公司 利用阿拉伯糖和碳酸亚乙酯使角蛋白纤维成形
MX2017016152A (es) 2015-06-18 2018-04-18 Procter & Gamble Modelado de fibras de queratina mediante el uso de compuestos de dialdehido.
WO2016205578A1 (en) * 2015-06-18 2016-12-22 The Procter & Gamble Company Shaping keratin fibres using 2-oxazolidinone compounds
AU2016318280B2 (en) 2015-09-08 2019-08-15 Kao Germany Gmbh Process for semipermanent straightening and permanent shaping hair
EP3383498A4 (en) * 2015-12-01 2019-08-14 ISP Investments LLC CAPILLARY CARE COMPOSITION, PREPARATION METHOD THEREOF, AND METHOD OF USE
WO2017096015A1 (en) * 2015-12-01 2017-06-08 Isp Investments Llc A hair care composition, process for preparing the same and method of use thereof
WO2018017408A1 (en) * 2016-07-18 2018-01-25 Isp Investments Llc A hair care composition, process for preparing the same and method of use thereof
GB201616657D0 (en) * 2016-09-30 2016-11-16 Innospec Ltd Methods, compositions and uses relating thereto
FR3061431B1 (fr) * 2016-12-29 2019-05-31 L'oreal Procede de traitement des fibres keratiniques mettant en oeuvre un derive de l'acide butenedioique et une silicone aminee
EP3573493A1 (en) 2017-01-26 2019-12-04 Lubrizol Advanced Materials, Inc. Hair styling appliances and methods of operating same
DE102017221630A1 (de) * 2017-12-01 2019-06-06 Henkel Ag & Co. Kgaa Restrukturierung von blondierten Haaren durch Mittel mit aliphatischen Polyolen und cyclischen Carbonaten
US11478412B2 (en) 2018-04-12 2022-10-25 Lubrizol Advanced Materials, Inc. Hair modification composition and method therefor
WO2021131915A1 (ja) * 2019-12-23 2021-07-01 花王株式会社 繊維処理剤組成物
WO2021224789A1 (en) * 2020-05-04 2021-11-11 Landa Labs (2012) Ltd. Compositions, kits and methods for styling hair fibers
US11173102B1 (en) 2020-05-31 2021-11-16 L'oreal Methods and compositions for removing color from color-treated hair
US11154479B1 (en) 2020-05-31 2021-10-26 L'oreal Methods of removing color from color-treated hair
KR102303467B1 (ko) * 2021-06-25 2021-09-23 인핸스비 주식회사 컬러 트리트먼트 및 샴푸용 조성물
US11363868B1 (en) * 2021-07-13 2022-06-21 Thalita Leite Curl-hair defining method
US12257331B2 (en) 2023-07-20 2025-03-25 L'oreal Methods for oxidatively bleaching or coloring hair without damaging the hair

Family Cites Families (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2873282A (en) 1952-04-05 1959-02-10 Jefferson Chem Co Inc Catalytic process for producing alkylene carbonates
US2798053A (en) 1952-09-03 1957-07-02 Goodrich Co B F Carboxylic polymers
US2773070A (en) 1952-10-31 1956-12-04 Jefferson Chem Co Inc Catalytic process for producing alkylene carbonates
US3657175A (en) 1969-06-26 1972-04-18 Standard Brands Chem Ind Inc Carboxylic acid latices providing unique thickening and dispersing agents
JPS5710085B2 (enrdf_load_stackoverflow) * 1973-05-04 1982-02-24
US3929678A (en) 1974-08-01 1975-12-30 Procter & Gamble Detergent composition having enhanced particulate soil removal performance
US4384096A (en) 1979-08-27 1983-05-17 The Dow Chemical Company Liquid emulsion polymers useful as pH responsive thickeners for aqueous systems
US4565647B1 (en) 1982-04-26 1994-04-05 Procter & Gamble Foaming surfactant compositions
US4509949A (en) 1983-06-13 1985-04-09 The B. F. Goodrich Company Water thickening agents consisting of copolymers of crosslinked acrylic acids and esters
US4464524A (en) 1983-07-26 1984-08-07 The Sherwin-Williams Company Polymeric thickeners and coatings containing same
US4801671A (en) 1987-06-25 1989-01-31 Desoto, Inc. Production of alkali-soluble, carboxyl-functional aqueous emulsion thickeners
US5087445A (en) 1989-09-08 1992-02-11 Richardson-Vicks, Inc. Photoprotection compositions having reduced dermal irritation
US5292843A (en) 1992-05-29 1994-03-08 Union Carbide Chemicals & Plastics Technology Corporation Polymers containing macromonomers
US5288814A (en) 1992-08-26 1994-02-22 The B. F. Goodrich Company Easy to disperse polycarboxylic acid thickeners
GB9320556D0 (en) 1993-10-06 1993-11-24 Unilever Plc Hair conditioning composition
US5858948A (en) 1996-05-03 1999-01-12 Procter & Gamble Company Liquid laundry detergent compositions comprising cotton soil release polymers and protease enzymes
US5968493A (en) 1997-10-28 1999-10-19 Amway Corportion Hair care composition
US6573375B2 (en) 2000-12-20 2003-06-03 Union Carbide Chemicals & Plastics Technology Corporation Liquid thickener for surfactant systems
US6384280B1 (en) * 2001-10-12 2002-05-07 Chevron Oronite Company Llc Process for the preparation of polyalkylphenoxyaminoalkanes
US7378479B2 (en) 2002-09-13 2008-05-27 Lubrizol Advanced Materials, Inc. Multi-purpose polymers, methods and compositions
FR2847473B1 (fr) 2002-11-25 2007-06-29 Expanscience Lab Composition comprenant au moins une oxazolidinone, son utilisation cosmetique et comme medicament
US7205271B2 (en) 2004-10-14 2007-04-17 Isp Investments Inc. Rheology modifier/hair styling resin
DE102005017913A1 (de) 2005-04-18 2006-10-26 Henkel Kgaa pastenförmige Haarbehandlungsmittel mit cyclischen Kohlensäureestern und Silikaten
JP4950487B2 (ja) 2005-12-26 2012-06-13 ライオン株式会社 ちぢれ毛矯正剤
EP1880710A1 (en) * 2006-07-21 2008-01-23 Wella Aktiengesellschaft Method and composition for permanently shaping hair
US8153109B2 (en) * 2006-11-21 2012-04-10 San-Ei Kagaku Co., Ltd. Alkylene carbonate dilution, alkylene carbonate for preparing the dilution, and aqueous reducing chemical agent
JP4370479B2 (ja) * 2006-11-21 2009-11-25 山栄化学株式会社 炭酸アルキレン希釈液及びパーマネントウェーブ１剤
JP2008231100A (ja) * 2007-02-20 2008-10-02 Fujifilm Corp 化粧料組成物、それを用いた光輝性美爪化粧料及び光輝性染毛化粧料
US8192729B2 (en) * 2009-12-21 2012-06-05 Robert Saute Composition and method for hair straightening
FR2978038B1 (fr) * 2011-07-19 2013-08-23 Oreal Procede de coloration des fibres keratiniques precede d'un traitement a base de liquide ionique
WO2013125053A1 (en) 2012-02-24 2013-08-29 L'oreal Process for treating keratin fibers
FR2988605B1 (fr) * 2012-03-27 2014-12-19 Oreal Procede de deformation et composition comprenant au moins 40% en poids de corps gras non silicones et au moins un agent epaississant mineral
US9463147B2 (en) * 2012-03-30 2016-10-11 Zotos International, Inc. Hair treatment and revitalizing composition and methods
US20160367462A1 (en) * 2013-06-07 2016-12-22 L'oreal Method of treating keratin matter by forming an ionic liquid

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022182596A1 (en) 2021-02-23 2022-09-01 Angus Chemical Company Substitution of ammonia in hair altering products

Also Published As

Publication number Publication date
US20150374604A1 (en) 2015-12-31
KR102197099B1 (ko) 2020-12-30
MX2015010160A (es) 2016-01-12
BR112015018706B1 (pt) 2020-04-22
CN105073090A (zh) 2015-11-18
WO2014123805A1 (en) 2014-08-14
US9872824B2 (en) 2018-01-23
EP2953610A1 (en) 2015-12-16
JP2016507528A (ja) 2016-03-10
CA2899597A1 (en) 2014-08-14
JP6452625B2 (ja) 2019-01-16
CN105073090B (zh) 2018-10-16
AU2014215569B2 (en) 2018-08-02
AU2014215569A1 (en) 2015-08-13
MX357773B (es) 2018-07-24
KR20150113206A (ko) 2015-10-07
BR112015018706A2 (pt) 2017-07-18

Similar Documents

Publication Publication Date Title
EP2953610B1 (en) Semi-permanent hair straightening composition and method
JP7377813B2 (ja) 毛髪改質組成物およびその方法
US20160296449A1 (en) Semi-Permanent Hair Straightening Composition And Method
JP5656990B2 (ja) 界面活性剤をベースとする系における改善された溶解性および性能を有するカチオン性合成ポリマー、ならびにパーソナルケアおよび家庭用用途における使用
US20130129639A1 (en) Cassia Derivatives
AU2019245317A1 (en) Hair styling compositions comprising polygalactomanans, and method for using the same
US20240238180A1 (en) Self-curing acrylic formulations containing n-acetyl cysteine for hair straightening
US12409120B2 (en) Process for permanent waving keratin fibers
US20230036311A1 (en) Process for permanent waving keratin fibers
JP2020200257A (ja) 毛髪変形剤第１剤、および毛髪変形方法
HK1221397B (zh) 用於处理头发的方法及其试剂盒

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20150828

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

AX Request for extension of the european patent

Extension state: BA ME

DAX Request for extension of the european patent (deleted)
STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: EXAMINATION IS IN PROGRESS

17Q First examination report despatched

Effective date: 20170127

GRAP Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOSNIGR1

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: GRANT OF PATENT IS INTENDED

INTG Intention to grant announced

Effective date: 20181001

GRAS Grant fee paid

Free format text: ORIGINAL CODE: EPIDOSNIGR3

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE PATENT HAS BEEN GRANTED

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

REG Reference to a national code

Ref country code: GB

Ref legal event code: FG4D

REG Reference to a national code

Ref country code: CH

Ref legal event code: EP

Ref country code: AT

Ref legal event code: REF

Ref document number: 1117711

Country of ref document: AT

Kind code of ref document: T

Effective date: 20190415

REG Reference to a national code

Ref country code: IE

Ref legal event code: FG4D

REG Reference to a national code

Ref country code: DE

Ref legal event code: R096

Ref document number: 602014044376

Country of ref document: DE

REG Reference to a national code

Ref country code: NL

Ref legal event code: MP

Effective date: 20190410

REG Reference to a national code

Ref country code: LT

Ref legal event code: MG4D

REG Reference to a national code

Ref country code: AT

Ref legal event code: MK05

Ref document number: 1117711

Country of ref document: AT

Kind code of ref document: T

Effective date: 20190410

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190410

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SE

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190410

Ref country code: LT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190410

Ref country code: AL

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190410

Ref country code: ES

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190410

Ref country code: NO

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190710

Ref country code: PT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190910

Ref country code: HR

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190410

Ref country code: FI

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190410

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: BG

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190710

Ref country code: GR

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190711

Ref country code: RS

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190410

Ref country code: LV

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190410

Ref country code: PL

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190410

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: IS

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190810

Ref country code: AT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190410

REG Reference to a national code

Ref country code: DE

Ref legal event code: R097

Ref document number: 602014044376

Country of ref document: DE

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: EE

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190410

Ref country code: DK

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190410

Ref country code: SK

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190410

Ref country code: CZ

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190410

Ref country code: RO

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190410

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SM

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190410

26N No opposition filed

Effective date: 20200113

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: TR

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190410

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GB

Payment date: 20200227

Year of fee payment: 7

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SI

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190410

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

REG Reference to a national code

Ref country code: BE

Ref legal event code: MM

Effective date: 20200229

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: MC

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190410

Ref country code: LU

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20200203

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: CH

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20200229

Ref country code: LI

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20200229

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: IE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20200203

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: BE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20200229

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 20210223

Year of fee payment: 8

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 20210225

Year of fee payment: 8

GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 20210203

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: IT

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20200203

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20210203

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: MT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190410

Ref country code: CY

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190410

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: MK

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20190410

REG Reference to a national code

Ref country code: DE

Ref legal event code: R119

Ref document number: 602014044376

Country of ref document: DE

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20220228

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20220901

P01 Opt-out of the competence of the unified patent court (upc) registered

Effective date: 20230426